US7951878B2ExpiredUtilityPatentIndex 41

Halogen-free flameproof epoxy resin formulations

Assignee: SCHILL & SEILACHER & LDQUO STRUKTOL & RDQUO AGPriority: Mar 31, 2006Filed: Dec 12, 2006Granted: May 31, 2011

Est. expiryMar 31, 2026(expired)· nominal 20-yr term from priority

Inventors:JUST BERTHOLD KELLER HOLGER DOERING MANFRED STORZER UWE SEIBOLD SEBASTIAN

C08G 59/4007C08G 59/3254H05K 1/0326H05K 2201/012

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Claims

Abstract

The invention relates to a method for preparing halogen-free flameproof epoxy resins, in which a halogen-free epoxy resin is reacted with a polyfunctional aldehyde or ketone and a phosphinic acid derivative, wherein the phosphinic acid derivative contains at least one P—H-active structural unit of the formula ═PH(O) and is used in an amount equivalent to the polyfunctionality of the aldehyde or ketone, to a halogen-free flameproof epoxy resin obtainable by this method, to the use of the epoxy resin as a base material for the manufacture of printed circuit boards and printed circuits and to intermediates used to prepare the epoxy resins.

Claims

exact text as granted — not AI-modified

1. A method for preparing halogen-free flameproof epoxy resins, in which a halogen-free epoxy resin is reacted with a polyfunctional aldehyde or ketone and a phosphinic acid derivative, wherein the phosphinic acid derivative contains at least one P—H-active structural unit of the formula ═PH(O) and is used in an amount equivalent to the polyfunctionality of the aldehyde or ketone.

2. The method of claim 1 wherein in a first step the polyfunctional aldehyde or the polyfunctional ketone is reacted with the phosphinic acid derivative to form a polyol, and in a second step said polyol is added to the epoxy resin.

3. The method of claim 1 wherein the epoxy resin is reacted in the presence of a catalyst.

4. The method of claim 3 , wherein a tertiary phosphane or amine or a salt thereof is used as a catalyst.

5. The method of claim 4 , wherein triphenylphosphine or triethanolamine is used as a catalyst.

6. The method of claim 1 , wherein the components are reacted at normal pressure and at a temperature between 100 and 160° C.

7. The method of claim 1 , wherein the flameproof epoxy resin obtained is cured using an amine curing agent.

8. The method of claim 7 , wherein the amine curing agent is selected from the group consisting of dicyandiamide, 1,1-dimethyl-3-phenyl urea, diethylene toluene diamine and a phenolic novolak.

9. A halogen-free flameproof epoxy resin obtained by reacting a halogenfree epoxy resin with a polyfunctional aldehyde or ketone and a phosphinic acid derivative, wherein the phosphinic acid derivative contains at least one P—H-active structural unit of the formula ═PH(O) and is used in an amount equivalent to the polyfunctionality of the aldehyde or ketone.

10. The epoxy resin of claim 9 , wherein the polyfunctional aldehyde or the polyfunctional ketone is a difunctional compound of the formula I,

wherein R is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group and R 1 is a substituted or unsubstituted alkylene or arylene group.

11. The epoxy resin of claim 10 , wherein the aldehyde or the ketone is selected from the group consisting of phthaldialdehyde, terephthaldialdehyde, isophthaldialdehyde and 1,4-diacetylbenzene.

12. The epoxy resin of claim 9 , wherein the halogen-free epoxy resin used as a starting material is a resin of the formula II,

wherein R 2 is the residue of substituted or unsubstituted bisphenylene methane, bisphenylene propane, a phenolic formaldehyde resin or novolak.

13. The epoxy resin of claim 9 , wherein the phosphinic acid derivative is a compound of the formulae Iva-IVe,

wherein R 3 and R 4 are independently a substituted or unsubstituted alkyl or aryl residue and
X=0, NH, N-alkyl, S, SO, SO 2 or Co.

14. The epoxy resin of claim 13 , wherein the phosphinic acid derivative is 9,10-dihydro-9-oxa-10-phospha-phenanthrene-10-oxide (DOPO).

15. The epoxy resin of claim 9 , having the formula

wherein R, R 1 and R 2 are each as defined in claim 9 , and “P” is the residue of a phosphinic acid derivative of one of the formulas Iva-IVe:

wherein R 3 and R 4 are independently a substituted or unsubstituted alkyl or aryl residue and
X=0, NH, N-alkyl, S, SO, SO 2 or Co, that is left after release of the hydrogen atom directly bound to the phosphorus atom.

16. The use of an epoxy resin of claim 9 as a base material for the manufacture of printed circuit boards and printed circuits.

17. An intermediate for the production of the epoxy resin of claim 10 obtained by the addition of a phosphinic acid derivative to a polyfunctional aldehyde or a polyfunctional ketone to form a polyol, wherein the phosphinic acid derivative contains at least one P—H-active structural unit of the formula ═PH(O) and is used in an amount equivalent to the polyfunctionality of the aldehyde or ketone.

18. The intermediate of claim 17 , wherein the polyfunctional aldehyde or the polyfunctional ketone is a difunctional compound of the formula I,

wherein R is a hydrogen atom or a substituted or unsubstituted alkyl or aryl group and R 1 is a substituted or unsubstituted alkylene or arylene group.

19. The intermediate of claim 18 , wherein the aldehyde or the ketone is selected from the group consisting of phthaldialdehyde, terephthaldialdehyde, isophthaldialdehyde and 1,4-diacetylbenzene.

20. The intermediate of claim 17 , wherein the phosphinic acid derivative is a compound of the formulas Iva-IVe,

wherein R 3 and R 4 are independently a substituted or unsubstituted alkyl or aryl residue and
X=0, NH, N-alkyl, 5, SO, SO 2 or CO.

21. The intermediate of claim 20 , wherein the phosphinic acid derivative is 9,10-dihydro-9-oxa-10-phospha-phenanthrene-10-oxide.

22. The method of claim 1 , wherein the components are reacted at normal pressure and at a temperature between 120 and 140 C.

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